Ethyl Acetate → 2-Methyl-1-[(R)-1-(2-methyl-4-nitro-phenyl)-pyrrolidin-3-ylamino]-propan-2-ol

HRID 69486

반응식

HRID 69486 반응식
[Li+].[Br-].[CH3:3][C:4]1([O:7][CH2:6]1)[CH3:5].F[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[N:18]1[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1.[C:24](OCC)(=O)C>CN1C(=O)CCC1.O>[CH3:3][C:4]([OH:7])([CH3:5])[CH2:6][NH:23][C@@H:20]1[CH2:21][CH2:22][N:18]([C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[CH3:24])[CH2:19]1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11208Isobutylene oxideHCID 82050Lithium BromideHCID 68687704(R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamine

생성물 1

HCID 689918962-Methyl-1-[(R)-1-(2-methyl-4-nitro-phenyl)-pyrrolidin-3-ylamino]-propan-2-ol

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

LiBr (153.6 mg) and isobutylene oxide (85.1 mg) were added to a solution of (R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamine (100 mg) in NMP (2 mL) and the reaction mixture was heated for 2 d at 80° C. Then ethyl acetate and water were added to the mixture. The aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 297.15 (C14H20FN3O3); MS (ESI): 298 (M+H+).

후처리

  1. extractionThe aqueous phase was extracted several times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was removed in vacuum
  4. customThe raw product was purified by preparative HPLC
  5. customIn this way the product was obtained with molecular weight 297.15 (C14H20FN3O3)

출처 및 근거

ORD 기록
ord-c9b57c8025e042e8b0831d2a6c1beb41
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

연결된 노트

불러오는 중…